The Personal Strategic Plan Inspired By a Harvard Business Legend

This five-step personal strategic planning exercise applies best practices from the business world to your life.


One of my favorite books I’ve read recently is How Will You Measure Your Life?

In it, Harvard Business School strategy guru Clayton Christensen applies his world-renowned theories to the business of living a good life. He looks to get to the bottom of this question:

Why have so many CEOs he’s known succeeded at business but run their personal lives to the ground?

The biggest reason: Self-help-ing yourself is way more boring than making billions. Big shot CEOs strategize business moves in meetings all day long, but never bother to fit any semblance of a personal strategic plan into their schedule. Eventually, their lives go kaput.

Christensen convinced me to try not to make the same mistake. So I followed the advice from his book and others like it—The 7 Habits of Highly Successful People, especially—to devise a personal strategic plan of my own.

I call it the “GPS” (general personal strategy).

It’s a five-step template that’s helped me figure out how to redirect my life toward not billions of dollars but more anti-regrets and an enjoyably fulfilling life.

General Personal Strategy (GPS) for [Insert Your Name Here]

To maximize My Life’s returns to (Step 1), I will optimize for (Step 2) and do some good by battling (Step 3). To do so more productively, I will release my handbrake of (Step 4.1) and replace it with (Step 4.2). And I am starting work on all of this immediately by (Step 5).

Personal Strategic Plan Step #1:

Think of Your Shareholders.

I like the perspective of looking at your life as if you’re the CEO of Your Life, Inc. You’re the head honcho responsible for delivering results to my shareholders.

Who are your shareholders?

Unless you got a bit ahead of yourself with the whole NFT craze and sold shares of yourself online, I’d argue your shareholders aren’t other people. Not even your kids or wife.

Your shareholders are future versions of you.

Imagine each Future You for every day left in your life has one voting share. They want themselves and the people they care about to be happy. Then ask yourself:

What action would the largest number of your thousands of shareholders vote in favor of?

Keep in mind that your shareholders understand what you’re incapable of. They won’t expect you to change the world in a day. Plus, they don’t want you to work so hard that it makes them miserable when it’s their turn to take the reins.

Today, it’s your turn. To be a better CEO, just try to be less selfish and more shareholder-friendly. Then tomorrow, it’s up to the next version of you to take over and do the same.

YouTube video

Personal Strategic Plan Step #2:

Define Your KPI

Ok, so you want to maximize long-term returns to your future selves, a.k.a. your shareholders.

What KPI (key performance indicator) are you using to measure how good or bad of a job you’re doing?

Consider this chart roughly approximating your life’s performance to date:

Your “Max Potential” is the absolute highest return you could possibly deliver to your shareholders in your lifetime. Time is your x-axis. And the big question is:

What’s your y-axis?

Happiness? Balance? Sense of community? Freedom? Buckets of Häagen-Dasz consumed?

There’s no easy answer. There’s not even a definitively correct answer. But it shouldn’t be too hard for you to come up with something better than what our monkey minds default to: money, sex, and power.

Even a rough KPI for your y-axis will help you make better long-run decisions. When in doubt, use it to ask yourself:

What action will direct me higher up my y-axis?

For example, I think my y-axis is “Growth.” So, by prioritizing growth over money, I decided to challenge myself to write this post instead of some money-grubbing article like, “Why starting a blog by using all these affiliate links will get you the passive-income life of your dreams.”

Personal Strategic Plan Step #3:

Pick Your Battle

This personal strategic planning step is triply counterintuitive, so lots of people skip it or screw it up.

Counter-intuition #1: To enjoy life, you need to struggle.

Without conflict, the story of your life will have no plot. And, as Donald Miller puts it in one of my favorite “sledgehammer” books, “If you aren’t telling a good story, nobody thinks you died too soon; they just think you died.”

To make matters worse, if you don’t pick your struggles, struggles you don’t want will find you.

Counter-intuition #2: Happiness doesn’t come from trying to make yourself happy but as a by-product of helping others get happier.

This is called the Hedonistic Paradox.

My favorite question for dealing with it and figuring out in what way you can help yourself by helping others is this:

What’s an injustice in the world that pisses you off and you’re willing and able to take on?

Counter-intuition #3: The best battles to pick are the ones you cannot win.

Rather than pick some dragon to slay, mountain to climb, or step-mom to hate, lick your finger, stick it in the air, and look for a headwind. It probably won’t ever stop blowing in your face, but you can harness it to make meaningful progress against it while enjoying the ride.

My battle, for example, is with the status quo and the social pressures and forces of complacency that support it. I’ll never defeat the status quo, but I’ve been having a wicked good time taking it on so far. And I like to think some people have benefitted from it.

What do you think your battle could be?

Cover image of me finding and releasing self-limiting beliefs
If only finding your handbrake of a self-limiting belief were so easy.

Personal Strategic Plan Step #4:

Release Your Handbrake

After the first three pie-in-the-sky personal strategic planning steps, it’s time to bring things back down to earth with this question:

What self-limiting belief holds you back from making more efficient progress?

This is your handbrake. Release it and your life will flow much more smoothly.

Step 4.1: Identify the limiting identity that’s your biggest handbrake.

Try these handbrake diagnostinacators:

  • What’s the most hurtful insult someone can give you?
    • e.g., If it stings when someone says, “You’re a coward,” it’s probably true. Or maybe you’re protecting some limiting identity of being perfect or successful by not taking more risks.
  • What fixed mindset could you replace with a growth mindset?
    • e.g., Thinking, “I’m smart.” That will make you defensive to evidence that you’re wrong and lead you to avoid challenging your self-perceived intelligence. Better to identify as “someone who likes to learn.”
  • When do you catch yourself saying, “I’m not _____ enough,” “I’m too _____,”  or “I suck at ______”?
    • e.g., “I’m too old to take on a personal strategic plan” means your age has become a limiting identity for you.
  • What are your biggest weaknesses?
    • If we were to survey your family members and colleagues, do you think they would say the same?

Step 4.2: Find an accelerating identity to put in its place.

A good accelerating identity:

  • Pushes you forward rather than holds you back.
  • Is consistent with your core values and inconsistent with the limiting identity you’re releasing.
  • Expands your potential rather than restricts it.
  • Is something you genuinely believe you can live up to.

The last point is worth emphasizing. No matter how many positive affirmations you perform, you can’t “be anything you want.” You’re not that genetically gifted.

For example, a limiting identity I used to have is “I’m antisocial.” Positively affirming, “I’m a people person,” in the mirror ten times every morning would never have worked. The more realistic maximizing identity that’s done the trick is to focus on being more of something I already was: “fun to be around.”

Now your turn. Come up with answers to Steps 4.1 and 4.1 and fill in the blanks:

I’m not going to be _____ anymore. I’m _____.

Zag Separator

Personal Strategic Plan Step #5:

Stop Planning and Get Started

Your personal strategic plan is nothing more than self-help fantasizing without this step.

Pull your head out of your butt and get moving by asking yourself:

What one small daily action step can you easily make the time to commit to doing to make your plan a reality?

To find your answer, let’s break this question down:

  • What one… What’s the single action you want to start with? Stick to one behavior change. Then, only when your comfort zone has expanded around it, add another. And so on. Keep it up and, before you know it, you’ll have incorporated dozens of improvements, and your comfort zone will be formidable.
  • …small daily habit…: What’s something so easy you could commit to keeping up for a whole year? Increase your odds of success by simply trying to do it for a week or two. One month, max.
  • …can you easily make the time…: What will you quit doing to free up time and energy for this new action? It has to fit into your lifestyle or it’ll inevitably get squeezed back out.
  • …to commit to doing…: When will you stop to assess whether or not this habit is moving you in the right direction? Maintain flexibililty to change direction instead of putting your head down until you smash into a dead end.
  • …to make your plan a reality: What habit contributes toward steps 1, 2, 3, and 4? Be consistent and coherent to be productive.

Once you have something in mind, ask yourself this:

How can I make this 10 percent more fun?

Do it with friends? Plan a celebration to reward yourself after doing it for a month?

Some Plan Is Better Than No Plan

Once again, here’s the GPS template with the five personal strategic plan components:

GPS for [Insert Your Name Here]

To optimize my life’s returns to my shareholders (Step 1), I will optimize for (Step 2) and do some good by battling (Step 3). To do so more productively, I will release my handbrake of (Step 4.1) and replace it with (Step 4.2). And I am starting work on all of this immediately by (Step 5).

Whether or not you decide to use this format doesn’t matter. It’s not like every CEO follows the same strategy, after all. You’re in charge of figuring out what works for you.

But, for your shareholders’ sake, hopefully the questions and explanations of each of the five steps have inspired you to prepare a personal strategic plan of your own. Better yet, use How Will You Measure Your Life as your resource.

Just plan something!

As long as you devise a strategy that gives you a slightly better sense of direction than before, move on it, review your progress, and update your plan accordingly, that’s progress.

How Will You Measure Your Life, by Clayton Christensen

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Cover image photo of Clayton Christensen adapted from Flickr.

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👋 I'm Chris. Everything you read on is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

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The Zag shares my adventures off of the boring beaten paths of life and ideas for finding your own unfollowable path.